1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-(2,6-diisopropylphenyl)-15-hydroxypentadecanamide

HRID 1532705

Reaktionsgleichung

Reaktionsgleichung von HRID 1532705
CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[OH:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][C:37]([OH:39])=O.[CH:40]([C:43]1[CH:49]=[CH:48][CH:47]=[C:46]([CH:50]([CH3:52])[CH3:51])[C:44]=1[NH2:45])([CH3:42])[CH3:41]>O.CN(C=O)C>[CH:50]([C:46]1[CH:47]=[CH:48][CH:49]=[C:43]([CH:40]([CH3:42])[CH3:41])[C:44]=1[NH:45][C:37](=[O:39])[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][OH:22])([CH3:52])[CH3:51]

Komponenten

7

Edukt 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 32484DiisopropylanilineHCID 757711-HydroxybenzotriazoleHCID 7836015-Hydroxypentadecanoic acid

Produkt 1

HCID 22633587N-(2,6-diisopropylphenyl)-15-hydroxypentadecanamideAusbeute 23 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

WSC (4.2 g, 22 mmols) and HOBt (3.0 g, 22 mmols) were added to a DMF (40 ml) solution of the resulting carboxylic acid (5.2 g, 20 mmols) and 2,6-diisopropylaniline (5.3 g, 30 mmols), and stirred at room temperature for 12 hours. Water was added to the reaction mixture, and the precipitate formed was taken out through filtration, and extracted with chloroform. The organic layer was washed with 1 N HCl and saturated saline in that order, and dried with anhydrous sodium sulfate, and the solvent was evaporated. The residue was extracted with ether and filtered, and the filtrate was concentrated under reduced pressure. The residue was purified through silica gel column chromatography (developer: hexane/acetone=5/1) to obtain 1.9 g (yield: 23%) of N-(2,6-diisopropylphenyl)-15-hydroxypentadecanamide.

Aufarbeitung

  1. customthe precipitate formed
  2. filtrationwas taken out through filtration
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with 1 N HCl and saturated saline in that order
  5. dry with materialdried with anhydrous sodium sulfate
  6. customthe solvent was evaporated
  7. extractionThe residue was extracted with ether
  8. filtrationfiltered
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customThe residue was purified through silica gel column chromatography (developer: hexane/acetone=5/1)

Quellen und Nachweise

ORD-Eintrag
ord-fa83c19b0a5141ab825ed46bbb25ab3f
Quelldatensatz
uspto-grants-2001_03
Patentnummer
US06204278B1

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